Having gone through several market cycles since being fully invested from 1988, both stock and real estate markets, I'd be cautious about expecting $8K per month in appreciation to continue indefinitely.

I am not planning on selling it but holding indefinitely… so right now I am not concerned about the capitals gains vs. stepped up basis.

Unfortunately he has a not so great personality and I couldn’t see myself working with him for an indefinite amount of time.

Depends on what state you’re trying to do your LLC in.

You don't have to have an indefinite outlook to work in engineering. 

I can quit my job tonight and still cover all of my living expenses indefinitely (living like a pauper but still more income than expenses) and that makes my day job much more enjoyable....I kind of just do what I want and I think I should be doing and if supervisors etc. don't agree ...well too bad for them I do what I want : ).

Real estate outside that where I can get real estate benefits for life and indefinitely defer the tax with 1031s.It strikes me that it is the changing of lanes that is more costly.

Always have a back up exit strategies since holding indefinitely is rarely realistic..

A Lot of agents 1) don’t really know all the intricacies/procedures/rules/strategies to do a short sale and 2) don’t want to do all the extra work involved in one, for no extra fees.Attorneys are not great for negotiating/processing shorts sales…they often slow the process down are not needed.If it comes to that point, have a talk with your agent, and their broker, about switching to an agent with short sale experience.You would need to show a financial hardship though….as in you can Not afford to pay the negative cash flow indefinitely. 

What determines whether or not you to continually recycle all of your money has more to do with how much value your able to generate with each deal... example: if you're able to acquire at a below market price then in crease it's value by 25%, then there are products which should allow you to recycle your money indefinitely.